


Strangers

by BornToRun91



Series: The Dean/Cas Multiverse [3]
Category: Supernatural
Genre: Alternate Universe - High School, Anxiety, Harvelle's Roadhouse (Supernatural), M/M, Nerd Castiel (Supernatural), Secret Crush, Self-Doubt, Self-Esteem Issues, Tutoring
Language: English
Status: In-Progress
Published: 2021-03-04
Updated: 2021-03-15
Packaged: 2021-03-17 04:21:21
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 20,306
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29835936
Author URL: https://archiveofourown.org/users/BornToRun91/pseuds/BornToRun91
Summary: Cas has been crushing on Dean, even though the two have never actually spoken to one another, but that's all about to change.Although this collection includes stories that all begin the same way, this one is a little bit than the previous.  Each story in this collection is a standalone story where Dean and Cas' personalities, their relationship to one another, and experiences are different.
Series: The Dean/Cas Multiverse [3]
Series URL: https://archiveofourown.org/series/2179428





	1. What Kind of Person Falls Asleep in Class?

**Summary for the Chapter:**

> With his friend Charlie, Cas talks about the frustrating dreams that he's been having lately.

Staring out the car window, Cas’ thoughts drifted away as he watched the loose leaves of autumn fly past; the sleek black Chevy Impala raced down the calm residential streets like an unstoppable force as some hairband rocked over the radio.

At the sound of Dean’s voice booming from the driver’s seat beside him, Cas couldn’t help but jump. He wasn’t sure how long Dean had been talking, trying to get his attention, but judging from his tone and heavily furrowed brow, Dean was clearly annoyed. “Dude, I’ve been talking to you for the last five minutes.” He paused for a moment, as though to let the guilt sink in. “What’s the last thing you heard?”

Dean wasn’t trying to hide his irritation, but even if he  _ did _ try, it wouldn’t have mattered; he and Cas had been friends long enough that Cas could pick up on the telltale signs of Dean’s frustration, no matter how subtle they may have seemed to anyone else.

“Sorry, Dean.” Cas watched as Dean shot him quick glances while trying to keep his attention on the road until Cas eventually allowed his gaze to drift back out the passenger window. He was met with the reflection of his own blue eyes staring back at him as the houses and trees rushed past in a blur. The silence between them was deafening, but what more did he need to say?

“Dude, where’s your head?” Although Cas continued to stare out the window, he could hear that Dean’s tone had changed and he imagined the furrowed brow relaxing.

They had driven another few blocks as Cas tried to figure out what he wanted to say. It wasn’t until he felt the car slow and finally stop that he turned his gaze back toward the driver’s seat.

Turning off the car, Dean removed the keys from the ignition and dropped them into the pocket of his worn leather jacket before turning on the bench seat to give Cas his full attention.

“Cas.” Dean’s voice was strong and almost impartial, but before Cas was able to offer a reply, Dean spoke again. “Castiel.”

Something was wrong. He could hear Dean, and yet his lips weren’t moving. “What is it, Dean?” At that moment, Cas’ heart began to race.

“Castiel!”

Someone was shaking him, jolting him awake. Unsure of what was happening, Cas overcompensated his movements and smacked his head against the metal tray that ran beneath the chalkboard; on top of everything else, he could add “seeing stars” to his list of troubles.

“Whoa, buddy. You alright?” He knew that Charlie was crouched down beside him, but he couldn’t see her clearly. His pulse quickened more--if that was even possible--as he tried to sit up further; what was wrong with his eyesight? Could he have a concussion? “Here,” Charlie said gently, placing his thick framed glasses on his face. “Cas, talk to me, babe. Are you okay?”

It took him a moment to remember where he was. It had been 8th hour and he was in English class; the sun had been shining through the window, and Cas’ desk sat perfectly in the warm, sunny rays. Mrs. Milton had been reading a short story by Shirley Jackson, her voice calm and pleasant, when he felt his eyes grow heavy.

“Charlie, where is everybody?” Cas’ voice was thick and raspy; he cleared his throat as he stretched, smacking his arm against the chalkboard and cursing under his breath.

Charlie’s eyebrows drooped slightly as she started grabbing his materials off of his desk and placing them into his backpack. “Class is over, Cas. Everybody packed up, and then the bell rang, but you kept sleeping.”

He was mortified. Not only had he  _ never _ fallen asleep in Mrs. Milton’s class before (he absolutely  _ loved _ her class), but he had never fallen asleep in  _ any _ class. “Oh shit. How upset is Milton?” English had always been his favorite subject, but even if it wasn’t, Mrs. Milton was the kind of teacher who could make anyone love her class; she had a sarcastic wit, she was pretty nerdy, and she treated her students like adults and not dumb little kids. The last thing Cas would ever want to do would be to disrespect his favorite teacher.

“She wasn’t mad. I was actually gonna wake you up when she finished reading the story, but she stopped me and told me not to. She said you were clearly having a hard time with somethin’ today.”

Cas closed his eyes and sighed. Just one more reason why she was his favorite teacher.

“Did you not sleep again last night?” Charlie had finished packing up all of Cas’ materials and plunked herself back into the desk next to him. She was, hands down, his best friend at school, so he had no problem confiding in her when these stupid dreams of his had started happening on a regular basis.

He sighed again. “I was up half the night. At first, I couldn’t fall asleep, and then when I did, I ended up waking up again after a couple hours, and that was that.” He had done the research; a person his age required, on average, seven to nine hours of sleep to be well-rested, and for the past couple weeks, he’d been getting a measly three to four.

“What was the dream about?”

Before Cas could answer, Mrs. Milton popped her head back in the room. “Everybody alright in here?” Her heavy blue frames framed her equally blue eyes, and even behind the glasses and thick black eyeliner, Cas could see the sparkle and the concern.

“I am so sorry, Mrs. Milton.” He rose from his seat, swinging his backpack onto his back while, once again, slamming his elbow against the chalkboard tray.  _ Fuck, that hurts _ .

She smiled. “Well, I appreciate it, Cas, but it’s alright. It’s not like you to fall asleep, so I figured something was going on. Plus, I mean, let’s be real here. Although you try hard to prove otherwise, you are only human. Sometimes things just catch up with us.” Her smile grew as she patted him on the arm.

Mrs. Milton was fairly young for a teacher, and although she was married with two kids, Cas always appreciated how she never dressed like any of the other female teachers in the building. Any chance she could, she came to school in jeans, a plaid shirt, and some kind of graphic t-shirt poking out at the collar, and that day was no different. While some people might say that she looked unprofessional, Cas thought she looked comfortable and more approachable, and if he would have asked any of his classmates, he would have bet that they’d say the same.

“Well, I do apologize and appreciate your understanding. It won’t happen again.” As Cas stood in the doorway, Charlie walked up beside him.

“I know, Cas. And Charlie? Keep an eye on him, alright?” She offered Charlie a simple smile, which Charlie answered with finger guns. “Now, you two get out of here and have a good night.”

“You too, Mrs. Milton,” Cas said as they walked out into the hall.

When they were far enough away, Charlie facepalmed herself and let out a grunt. “The fuck did I use finger guns for?” The overdramatic whine that escaped her lips made Cas smile. “She’s so awesome, but I get all weird when she talks to me.” Dropping her hand, she looked back at Cas, but her face was still contorted in embarrassment. “Castiel Novak, don’t  _ ever _ get a crush on a teacher.”

Cas offered a smile, but it was a weak attempt. “Oh, you don’t have to worry about that.”

“Aww, shit. Sorry, Cas. Go back to your dream. What happened?”

As they walked out of the school, the humid September air hit them instantly. No wonder he fell asleep in class; these days felt like an extension of the warm and inviting summer that had just barely ended for them.

“Okay. Last night, I dreamt that we were playing for pep band at one of the basketball games, and Dean was with us and also played alto. Well, he said that he did not have his flip folder or any of his music, so he had to share with me. But, to see, he had to stand over my shoulder, and I could feel him there the entire time, and when we were playing ‘Hey, Baby!’ he and I actually sang to each other, and he put his arm around me. I don’t know, Charlie. It was weird, and then after I woke up, I started going all Freud to try and figure out what it all meant.” Cas and Charlie sat at one of the tables outside of the school, soaking up the warmth and prolonging the walk home.

“Yeah, that’s weird.” She bit her lip. “I wish I paid more attention in psychology, because I don’t have the slightest clue how to psychoanalyze that.”

“And then when I fell asleep in class,” Cas continued, needing to get everything off of his chest, “it was that one in the car again. Like, we never talk much in that dream, but I can  _ feel _ that we’re friends and that we know one another.”

Charlie let her eyes drift towards the street. She bit her cheek slightly and ran a hand over her mouth. “How many classes do you have with him this year?”

He held up a single finger in response. “APUSH.” A.P. U.S. History was his first class after lunch which was convenient as his classroom was located immediately outside of the cafeteria. He had always enjoyed history, and any class taught by Ms. Mills was sure to be enjoyable, but on the first day of the school year, as Cas sat in a desk towards the center of the room, he watched as Dean Winchester walked through the doors, and at that moment, he could have fainted. All Dean’s badass-ness was just too much, and to Cas’ horror  _ and _ excitement, Dean took the seat immediately in front of him. Although the back of his head wasn’t the most appealing side of Dean, Cas would not complain. The proximity allowed him to hear the rumble of his voice and the joy behind his laugh; he could smell Dean’s body wash which Cas thought smelled like rainforest, although he didn’t know what a rainforest actually smelled like. From where he sat, he was also lucky enough to watch Dean run his fingers through his hair absentmindedly. Somehow, even that small action made his heart flutter.

As much as Cas was in heaven during that class, that was also the first night that the dreams had started. Since then, Cas had not gotten a restful night’s sleep, so one could argue that being in Dan’s presence was also becoming Cas’ own personal hell.

“Have you talked to him at all yet?” From how she asked the question, Charlie clearly already knew the answer, but bless her little heart for trying nonetheless.

Cas dropped his head and shook it solemnly. “Last week, Dean had turned to talk to Lee Webb before class, and the two were both  _ very _ animated with their conversation and hand gestures, and Dean bumped my pencil off my desk.” He let out a sigh. “When he realized what he did, he apologized and picked it up for me, but when he offered it back, I froze and didn’t take it. Like an idiot, I sat there and looked at him until he eventually chuckled a little and just put it back for me.”

“Yeah, that’s rough.” Cas rolled his eyes.  _ Well, wasn’t that the understatement of the year _ . “So, what I think you should do, Cas, is talk to the guy.”

Although he thought he had spoken clearly, Charlie must have misunderstood him before, because she  _ obviously _ missed the part where he explained that he could not will himself to speak with Dean Winchester, even when the boy initiated contact. How was Cas going to ever strike up the conversation himself?


	2. Taking a Tumble

**Summary for the Chapter:**

> Dean gets to school early to talk to his history teacher, only to run into one of his classmates in the hallway.

“Sammy, get your ass out of bed! We gotta go!” Dean had been awake for over an hour already. Although they still had over an hour and a half before school started, he also knew that his little brother’s shower and hair routines took hella longer than were really needed.

Grumbling, Sam Winchester stepped out of his bedroom, rubbing at his eyes, his long brown hair sticking up every which way. “Dean,” he began, not even trying to stifle his yawn, “it’s only six.” He rubbed his stomach with one hand as the other scratched at the back of his head.

“No shit, Sherlock, but you need to get a move on. I’ve gotta go talk to Ms. Mills before first hour, and I’m not going to be late because of your hair.”

Sam rolled his eyes and walked back into his bedroom. Within a minute, he was traipsing back down the hall with his towel and clothes in hand.

Dean chuckled to himself as he drained what was left of his Mountain Dew. Since he woke up, he’d gotten himself ready, made and ate breakfast, started the dishwasher, and enjoyed his first can of the day. He contemplated cracking open another, but decided against it; when he had too many in the morning, he always felt super jittery throughout the day and like his heart was going to break from his chest.

Although his bathroom routine was significantly longer than Dean’s, Sam was cleaned and styled before 6:30. Dean loved giving his little brother a hard time just for shits and giggles, but he had also learned long ago that comments like that ensured that Sam got his shit done quick, even if only to prove a point.

Standing in the kitchen entryway, Sam held out his arms as though trying to prove something impressive, although his face was blank. “There, jerk. You’ve got plenty of time to figure out whatever you need.”

“Yeah, yeah, bitch. Grab your bag and let’s go.” Sam rolled his eyes again, but did as he was directed.

Dean was already out in the Impala with the engine running as his baby brother locked the front door behind him and ran down to the passenger side door. What Sam didn’t realize, though, was that Dean already had the car in reverse, so as Sam reached for the lever, Dean started to roll backwards down the driveway. He only got a few feet before he stopped, laughing at his brother. Oh, if looks could kill, Dean would have been a goner.

“Are you fucking nine now, Dean?” To Sam’s visible frustration, Dean repeated this twice before finally letting his brother get into the car and hitting the road.

As they pulled into the parking lot, Sam was no longer scowling at his older brother, but Dean knew that he wasn’t over it; Sam would try to get him back eventually.

Walking towards the school doors, he glanced once more at his baby parked in the lot before entering the building. Although it was ten minutes to seven, the halls were already filled with bustling students and unnecessarily loud voices.

As he arrived at Ms. Milton’s room, he saw that her classroom door was partially closed. Peeking through the small window, he could see that she was busy talking with another student, so Dean leaned against the wall outside her room and waited. As he did, he started thinking about upcoming things on his schedule. Homecoming was already a couple weeks away. This was the first year that he had decided not to play football--his senior year of all years, much to his father’s dismay--but he was looking forward to going to the game anyways and cheering on his former teammates. Spending a Friday night anywhere but at a football stadium in the months of September through November was, like, sinful, even if he wasn’t suiting up to play. But the Homecoming festivities didn’t end with the game.

After their team undoubtedly kicked ass, everybody would be looking to celebrate and get shit faced. Contrary to popular belief, though, Dean wasn’t much of a partier, so he’d probably just go home after the game and relax, but Saturday was the dance, and Dean loved any opportunity to dress in a monkey suit like his favorite double-0 agent. As a sophomore, he had decided to buy a tux instead of always renting, and after his second time wearing it, the purchase had paid for itself. He may have grown some since 10th grade, but damn, did he still look good. Before the dance, he and his friends were all going to go to dinner, but he wasn’t sure what had been decided; he’d have to remember to ask Jo.

Just then, Ms. Mills’ door opened. The student left the room, walking backwards and continuing to speak as he went, until he ended up slamming into Dean. In a mass of arms, legs, and backpacks, the two boys fell to the ground in a heap.

“Oh my gosh, I’m so sorry,” the other boy said. Sitting himself up, Dean started collecting the papers that had been dropped as the other student squinted, hands outstretched, clearly looking for a pair of glasses. Feeling bad for the guy, Dean paused what he was doing and scanned the floor around him before finding a thick black pair of glasses near his feet. As he reached for them, he was glad to see that they were unharmed, and he turned towards the other boy who was still fumbling around, now looking a little more frazzled than before.

“Hey, here ya go.” Dean held out the glasses, but realizing that the other kid’s depth perception was clearly a mess, he instead grabbed the boy’s arm with one hand and held out the glasses with his other.

“Oh, wow, thank you.” As the kid put the glasses on his face, they made eye contact for the first time and Dean realized that he’d met this kid before.

“Hey, you’re in class with me, right?” But Dean’s question was left unanswered. Instead, the other boy sat with his mouth open, reminding Dean a lot of those weird singing Billy Bass fish that people used to have in their houses. “Dude, you alright?” Again, the other kid didn’t answer, but Dean didn’t let it phase him.

Pushing himself to his feet, he grabbed the pile of papers that he had been collecting and then offered his free hand to the kid on the floor. When the boy remained where he sat, his gaze still on Dean, Dean rolled his eyes and pulled the kid up.

That was all the other boy needed to snap him out of whatever was going on in his head. “I am really very sorry,” he muttered quickly.

“Nah, don’t worry about it,” Dean replied. “You sit behind me in Mills’ class, right?” In response, the other boy nodded, his eyes still staring at his feet. “Yeah, I thought so. My name’s Dean, by the way.”

At this, the other boy’s face went scarlet. “Castiel. M--my name’s Castiel.” His voice was no more than a whisper.

“Castiel.” Dean shrugged. “That’s one I’ve never heard before. Well, Castiel, I think these are yours.” He handed the papers back over, and watched as a timid hand was extended to take them.

Although Castiel’s voice had been quiet before, it was now no louder than a whisper. “Thank you, Dean.” And with that, Castiel bent down to pick up his backpack and hurried on his way.

Dean watched the other kid round the corner before he bent over to pick up his own backpack, noticing then the pencil case that was left on the floor. On one side of the cloth case, in neat and immaculate writing, were the words, “If found, return to Castiel Novak;” beneath that, in a style that was far less formal, it said, “Cas loves Charlie.”

“Cas,” Dean said to himself. Tucking the pencil case under his arm, he gave Ms. Mills door a small knock before walking in with a big cheesy smile on his face.

“Well, well, well. If it isn’t my second favorite Winchester.” Ms. Mills had been standing beside her desk flipping through a pile of papers as Dean walked in, but abandoned what she was doing to give Dean her attention.

“Come on, Mills. You don’t even have my brother,” he smirked.

“Yeah, so what does that say about you?” She smiled at him as he sat himself down on top of the desk immediately in front of hers. “What can I do for you?”

Over the next few minutes, Dean explained how he was already feeling a little overwhelmed with the work for class (he was paying attention, doing all the readings, and taking notes, but early U.S. history had always been tough for him), so he was hoping he could get some extra help.

She looked at him thoughtfully, as though racking her brain for ways to help, before a lightbulb seemed to go on. “Alright, yeah. One of your classmates, Castiel Novak--he was actually the one I was talking to before you--he has been willing to do some tutoring in years past. Why don’t we ask him? Would you be comfortable with that?”

Dean wasn’t above working with a tutor, whether that tutor be a student or a teacher, but that Cas kid seemed a little out of it in the couple times he’d tried to talk to him. But, he trusted Ms. Mills, so he thanked her for the suggestion and left the room.


	3. Crispitos

**Summary for the Chapter:**

> Cas reflects on that morning's incident with Dean, and for better or worse, he is able to talk about his feelings with a couple of his classmates.

First hour ended at 8:25, but their band director always let them pack up early to get their instruments and music put away before the bell rang. As Charlie and Cas were crouched together in front of their shared band locker, disassembling their saxophones and putting them in their cases, they spoke in quick, hushed voices.

“Are you kidding me?” Charlie’s eyes were bulging, threatening to pop out of her skull. It would have looked comical if Cas’ expression hadn’t been identical.

“I was mortified-- _ am _ mortified!” He could feel his cheeks begin to burn and his hands shook slightly. Even though it had been over an hour since his ordeal with the gorgeous Dean Winchester, Cas had found that his brain (and his hands) were both less than cooperative. For most of band class, he had chosen to go through the motions of playing without ever actually blowing into his instrument; on the few occasions when he did have to play, he was appalled by the squeaks and incorrect notes that his instrument created.

“Like, did he  _ actually _ fall though?”

“Charlie, I knocked him to the ground and sent our materials tumbling down the hallway.” Although that last part was a bit of an exaggeration, the overall statement was true.

“What did he say?” Her hushed voice had grown progressively louder the more excited that she was feeling, and at this point, she was clearly very excited.

“He--” Cas paused, thinking back to the incident; it was a painful memory, and his face reflected the pain that he was feeling. “He gave me back my glasses, and said I looked familiar, and introduced himself-- _ as though I haven’t been in love with him for years! _ \--and asked me my name, but I just froze like a schmuck, so he offered me a hand to pull me up, but I still couldn’t get myself to move or blink or breathe, so he eventually just pulled me up and gave me back my things!” The words flew from his mouth in a single breath. Although his eyes were closed as he spoke, thinking back to the mortification that he had experienced, he opened them after he finished speaking and saw Charlie staring back at him, her mouth agape. “That’s the same face that I made at him!” In the overdramatic fashion that he only allowed himself to display when he was with Charlie, Cas flopped on the floor as his friend rubbed his back.

“Well,” she said gently, “I’m glad you took my advice.” Cas looked up at her, confusion etched across his face. “I told you to talk to the guy!”

With a whimper, he dropped his head back to the floor, wishing that a quick death would find him.

  
  


Second and third hours went by with no additional mishaps, although he felt incomplete without his pencil case. Cas was typically so organized, so he wasn’t sure how he could have misplaced it, especially when it held all of the colored pens and highlighters that were a crucial part of his neat and orderly note taking.

He walked into the cafeteria for fourth hour and plunked himself down at his typical table, placing his backpack neatly beneath his chair. He’d decided that he’d make a trip to his locker before APUSH to check for his pencil case, but for now, he was starving. He had gotten up earlier than normal that morning to talk with Ms. Mills, so he skipped out on his usual bagel and fruit cup for breakfast.

Without waiting for Charlie, he gave his school ID card a pat in his pocket and then made his way to the end of the line. Although he did not typically enjoy cafeteria food, there were crispitos available that day. How could  _ anyone _ in their right mind turn down crispitos?

The line snaked from one end of the cafeteria to the other, but moved rather quickly. Within 10 minutes, Cas was on his way back to his table with two helpings of crispitos (for God’s sake, they’re  _ crispitos _ !) when he saw someone sitting on his table with their back to him. From a distance, he couldn’t tell who they were, but as he got closer, he watched as the figure ran their fingers through their sandy brown hair in a way that Cas knew all too well. And in that instance, he knew. Dean Winchester. As the realization set in, Cas found himself unable to move his feet any further. He had awkwardly stopped midstep, only a few yards away from his table. What was he supposed to do? Should he leave his backpack and run from the cafeteria? Maybe just leave the building? Was receiving a high school diploma  _ really _ that important to his future at this point?

As the thoughts tumbled around his head, he heard a few voices whisper around him, although he had no idea what was being said or who it was all being said to; however, the voices drew the attention of one very handsome senior who stole a glance over his shoulder and locked eyes with Cas.

“Hey, Cas.” Dean hopped off the table in a fluid and flawless movement that made Cas’ head hurt and heart flutter. “Remember me?” Cas knew that he should talk--really, he did--but he had not been able to make a sound or move closer to his table. Dean seemed to notice the effect that he had on him. “I’ll take that as a yes.” He smiled. “Mind if I sit here?” He gestured to the seat beside Cas’ own chair, but never waited for a reply.

Seeing that Dean was clearly waiting to speak with him, but also because his lunch tray was growing heavier by the minute, Cas fought hard to move his feet forward, one step at a time, until he reached his table. With shaking hands, he slowly put down his lunch, carefully slid his own chair back, and lowered himself onto his seat. Taking a few calming breaths (at that moment, no such breath actually existed for Cas), he turned to look at Dean. He didn’t know what could have prompted this impromptu visit (g _ ah! _ Even his thoughts were behaving ridiculously!), but he assumed it was because Cas had been an absolute klutz that morning.

Finding his voice and doing his best to keep it under control, Cas spoke quietly yet quickly. “I am very sorry for this morning. I was foolishly trying to multitask--one should be able to walk and talk simultaneously, but I clearly cannot--and I was not looking where I was going. Truly, I am very sorry. The last thing I would have wanted to do was to harm your reputation in any way or make you seem inept, because you are far from inept, let me assure you. And if I harmed you in any way--not like I think I’m stronger than you, because I am well aware that I’m not. I mean, you’re so strong and muscular and...uhm, strong.” He felt his face burn and again fought the urge to sprint from the building. Looking Dean in the eyes was painful, and yet he could not look away, so he simply sat there, silent once again.

Dean seemed a little unsure of what to say, instead giving a small chuckle and shaking his head as though Cas’ words were pestering flies who dared to bother him. “Dude, enough with the self-deprecation.” Although the words seemed scolding, Dean’s tone and mannerisms did not; if anything, he seemed concerned and bothered. “Accidents happen, alright? I was the goof standing in the hallway and not paying attention, so I’m just as much at fault. Plus, I don’t know what you’re going on about with my reputation. I do enough dumb shit on my own to mess with that, so you don’t worry.”

Finally, Cas broke eye contact and instead looked down at his tray, nodding slightly as he did. All day, his thoughts had been about how embarrassed he was over what happened, but deep down, he had also been afraid that he’d done harm to Dean’s image or popularity. Some people take that very seriously, and from everything Cas knew, Dean was the kind of person who would have been  _ very _ concerned; it was high school, after all.

“Anywho, now that that’s cleared up, I wanted to talk to you about APUSH.” Cas lifted his head, meeting Dean’s gaze and raising an eyebrow in the process. “I had gone to talk to Ms. Mills about getting some help for class, and she told me that you’re super smart and have actually tutored people in other years, so I was wondering if you could maybe help me out with stuff for our class.” Dean paused briefly, allowing Cas to consider what had been said. “I want to get a good score on the AP test, but early U.S. history just really confuses me.”

“Uhm, yes. Ab--absolutely.” This was the first time that he had responded to Dean in a timely fashion and without overthinking. In fact, his quick response seemed just as surprising to Dean as it did to himself.

“Wow, thanks. And I had this whole thing planned where I was going to offer to buy you food or something to persuade you.” At this, Cas’ eyes got wider and Dean smiled again, hitting him playfully on the arm. “Dude, you got to breathe, alright?”

_ He touched me, he touched me, he touched me, he touched my fucking shoulder, he touched me, he…. _ “Yeah, sorry, Dean.”

“And again with the apologies!” Although Dean smiled, his voice got loud and he again seemed annoyed. “Cas, can I be frank with you?” His voice was lower now, below even a typical conversational volume, and he leaned towards Cas as he spoke. Accepting the brief nod as a sufficient response, Dean continued in hushed tones, “I really appreciate you being willing to help me, for real. Like, I was stressed this morning, felt a little more relieved when Mills suggested that I talk to you, but now feel so much better that you agreed, so really, thank you.” Cas wasn’t sure if he was supposed to respond or not, but he gave a slight nod of the head.

As it turned out, though, Dean Winchester was not done speaking. “Now,” again, his voice dropped lower so now even Cas was leaning forward to hear, “if I’m wrong, say so, but I get this feeling that you’ve got a thing for me.”  _ Warning: brain will self-destruct in T-minus 10, 9, 8…. _ Cas had felt all kinds of embarrassed since 7 o’clock that morning, but this was the first point that he felt as though he may actually throw up. Not only was he talking to  _ Dean _ and had he agreed to tutor  _ Dean _ , but  _ Dean _ was talking to him about the crush he had on him. If he had been able to see himself, he’d have imagined that the bright red face he’d been wearing since he first saw Dean at his table had since faded to ghastly white, or maybe even a nice seafoam green. Either way, he could feel perspiration forming at his hairline and, somehow, even his glasses began to fog up slightly.

His voice lighthearted, Dean joked, “I’m getting this feeling that you’re not one for talking, Cas.” Cas allowed his head to fall towards the table, and like the fool that he was, he didn’t make sure that his arms were there to lessen the impact. Cas’ head hit the table with a  _ thud _ as Dean gave a chuckle. “Okay, okay.” Dean’s laugh was not what Cas had been anticipating; it was full and genuine, with no hint of mockery or malice. “Hey, can you pick your head up real quick?” Again with the hushed whisper.

Cas did as he was asked, allowing his gaze to lock onto Dean’s. He felt physically and emotionally exhausted, and damn, the day wasn’t even half over yet. “Straight up, Cas: are you comfortable tutoring me? Because if not, man, I totally get it. No hard feelings, I promise.”

At this, Cas sat up straighter. “No, I--I have no problems with this, Dean.”

Dean nodded, seeming to assess Cas’ response as he did so. “Cool. Okay, so, I’d like to talk about this real quick then, if you don’t mind.” He gestured between the two of them, but didn’t wait for Cas to reply. “The last thing I want to do is make you uncomfortable, alright? Now or in the future.” Cas nodded slowly in understanding. “Alright, cool. So, maybe I’m wrong, but I don’t think I am here, but I think you have a crush on me--” Cas was hanging his head again as Dean reached over quickly and took hold of his shoulder, dropping his gaze until their eyes met again “--but it’s not a big deal, okay? Like, I don’t want you to feel awkward or embarrassed or whatever.” Staring into those bright green eyes, Cas saw nothing but honesty. If any part of him still worried that Dean had some evil or ulterior motive, the look in his eyes would have quickly quelled those fears, so Cas gave a small, understanding nod.

Dean smiled as his voice returned to a normal volume. “Rock on. Well, I realize that I took up most of your lunch--my bad--and I gotta go get food myself, so I’ll let you eat and I’ll see you in class.” Again he patted Cas on the shoulder as he offered a smile before turning towards the lunch line. Before making it four steps, though, the door of the lines closed, signifying that they were no longer serving meals.

Dean gave a sigh before doing an about-face and turning towards Cas once again. Shrugging his shoulders, he walked back to the seat that he had vacated. “You mind if I just chill with you until the bell rings?” to which Cas gestured towards the seat next to him.

Staring down at his tray, Cas remembered then that he had purchased two orders of crispitos that day. “Uhm, they’ll be cold and less appetizing, but would you like one of these?”

Dean smiled. “Nah, man. You eat those. I mean, come on, they’re crispitos!”

For the first time in Dean’s presence, Cas smiled unabashedly. “That was my exact thought when I ordered two, but I made an overzealous purchase and would like you to eat them. Please.” He handed one of the trays over, and although he still seemed hesitant, Dean’s stomach took the opportunity to let out a grumble and he laughed to himself as he took the food.

“Thanks, man.”


	4. Conversation in the LMC

**Summary for the Chapter:**

> Cas and Dean have their first tutoring session in the LMC after school, but things don't go as planned.

Before the end of lunch, Dean could tell that Cas had grown a little more comfortable, at least to the point of being able to have a conversation. Yeah, he still noticed that Cas watched his lips intently as he spoke, and when Dean asked him questions about his life, Cas’ face would grow bright red as though he couldn’t fathom how or why Dean would care enough to ask, but it was still a definite improvement.

“Say again?”

Cas’ cheeks flushed as he gave an embarrassed grin. “I said my brothers and I were all named after angels. Well, mostly. I’m Castiel James, and my brothers are Michael Adam, Lucas Nicholas, and Gabriel Richard. Technically, Luke’s name was inspired by the angel  _ Lucifer _ , and we’re all thankful that my parents chose to make that change.”

Dean couldn’t hide his smile. “Dude, that’s pretty sweet. But you know, I’ve been calling you ‘Cas,’ and I don’t even know if that’s alright. My bad.” Dean’s smile had faded some, and was replaced with a look of genuine care. “Is that alright--or better yet, what do you want to be called?”

“You know, Dean, I don’t know the last time someone asked me that.” Cas’ features were soft and he looked very pleased. As he noticed this, Dean couldn’t help but feel good; the kid spent enough time looking all mortified. “I do prefer Cas, and I appreciate you asking. Two of my brothers--Gabe and Luke--also go by shortened versions of their names; it’s only our oldest brother Michael who seems to think a nickname is beneath him.”

“With a name like ‘Dean,’ you don’t really have much room for a nickname. My brother’s name is Sam--er, it’s actually Samuel, but  _ nobody _ calls him that--but I call him Sammy. He absolutely hates it, but being the big brother, he lets it slide.” Dean felt his chest swell with pride as he thought about his little brother. No matter what he was talking about or what was going on, Dean loved being able to talk about and brag about Sam. “He can be a little bitch sometimes, but damn, I love the kid.”

Cas smiled as the bell rang. Dean collected their trash from the table and walked it over to the garbage can as Cas grabbed his backpack, carefully pushing in both of their seats.

“Off to APUSH!” Dean called, as though he were triumphantly claiming land for the crown.

“I, uhm, have to stop at my locker before class.” Cas had frozen right outside of the cafeteria, directing his body towards the side staircase. “It’s just up on the second floor, but I’ll see you in class. And thank you for the company, Dean.”

Dean stood back as Cas meandered through the traffic of students towards the staircase. As Cas began his ascent, Dean started making his way that direction as well. He never brought his backpack with him to the lunch room (why bother when it’s just going to take up space?), so he needed to retrieve it and the rest of his materials before fifth period.

Dean was thankful that his locker was right at the top of the stairs and in a fairly centralized spot within the school. With three quick spins of the dial, the locker was open and he was grabbing what he needed when he suddenly remembered that he had Cas’ pencil case. He fished the zipper pouch out of his backpack and tucked it under his arm before throwing his bag on his back and closing his locker. He gave the dial a few more quick spins, and then made his way back downstairs.

The students had seven minute passing time, which was way more than he needed, so he made a quick pit stop at the bathroom right outside the cafeteria before traveling the short distance down the main hallway to Ms. Mills’ room. He was just about to enter the class when he saw Cas’ messy black head of hair walking his direction. Dean wasn’t sure what had happened in the few minutes since he’d seen him, but Cas’ head was down and his shoulders were hunched.

“Hey, Cas, what’s going on?”

Cas stopped abruptly, his face slightly contorted with a look of confusion. When he spoke, Dean noticed that his voice had returned to the shy speech that he so often used around Dean. “It’s silly, I know, but I can’t find my pencil case. It has all of my supplies for note taking and such. I’ve been trying to retrace my steps, and I don’t remember taking it out of my backpack yesterday, but I cannot find it anywhere.” In addition to his voice being soft, he was also speaking quickly and his eyes seemed to dart from side to side without focusing on anything in particular.

“Aww, man, my bad. I didn’t know that’s what you went looking for.” Dean took the pencil case out from under his arm and offered it to Cas. “You left so quickly this morning, and this was still on the ground. I didn’t bring it to lunch, but was gonna give it back to you during Mills’ class. I’m sorry, man.”

With the look of relief on Cas’ face, you’d think a future of student debt forgiveness had been offered to him. Not only did he sigh and relax his shoulders, but he gave a huge smile as he tilted his head. “Oh, Dean, thank you! Truly, you’re a lifesaver.” This made Dean smile. He patted Cas on the arm, and left his hand there to guide him into the classroom. As he did, he felt a rigidity return to Cas’ shoulder, but Dean ignored it and continued to smile. 

Class was nothing special. Before the hour started, Dean took the time to introduce Lee Webb to Cas; although they had all been in school together since at least middle school, their circles didn’t typically overlap, and he didn’t doubt that Lee would have no clue who Cas was. After doing quick “hey, how ya doin’?”s, Mills started her lecture. Although they had been given a little time during the hour to take a break to chat or be on their phones, things otherwise went fairly quick. In fact, Mills was so impressed with how attentive and on-point everybody was that she let them pack up about 10 minutes early. This was so uncharacteristic of her, but Dean learned never to question a teacher when they’re doing something spontaneous and nice.

Seats were turned and phones came out as the room started getting a little louder; all it took was one quick volume reminder from Ms. Mills, and then all was well.

Immediately, Dean turned to Lee. They spent a couple minutes talking about the homecoming football game; Lee was a wide receiver, and even though Dean wasn’t playing anymore, he still loved to talk shop. When their conversation lulled, however, Dean caught sight of Cas silently sitting at the desk just behind him, his seat unmoved, with his chin rested on his hands and his eyes closed. It almost looked like he could be sleeping, but after a gentle poke to the arm and a flinch from Cas, Dean was sure that he had been awake the entire time.

“Hey, man, you good?” He, again, couldn’t hide the smirk as he watched the crystal-clear blue eyes adjust and focus before Cas seemed ready to speak.

“Oh, Dean. I’m sorry.” Cas blinked hard a couple times as he sat up.

“Cas, come on. Stop with the apologies. Just wanted to make sure that you were alright. Mills never gives us time like this, and here you are, all zoned out.” Dean watched as Cas glanced around the room, taking in their surroundings; while he waited for a response, Dean did the same. At that moment, their classmates were either absorbed in conversations or on their phones. Even Lee had turned his attention away and was talking to somebody else. When Cas finally looked back towards Dean, he gave a nervous adjustment to his thick black frames and dropped his eyes to his desk. Dean then made a mental note that Cas’ self-esteem seemed to be for shit, or at the very least, just not great.

Cas rubbed a finger against the tip of his nose. “No, I’m alright, but, uh, thank you for asking.”

When Dean realized that he wasn’t getting more of an answer, he tried a different route to get their conversation going. “Fair enough. While I’m thinking about it, are you still alright helping me with APUSH?” Cas’ eyebrows went up as he gave a gentle smile and nod of the head. “Rock on. So, here’s the tricky part to that. I don’t have a study hall this semester. Are you ever available after school?”

“Uh….” Cas sat in his seat, his expression empty and his mouth hanging slightly open. When he didn’t immediately respond, Dean decided to let the silence fall between them, but he never broke eye contact. Finally, Cas seemed to find the words. “I, uh--yes, I’m available after school.”

“Perfect.” Dean smiled again. “What day works for you?”

“I mean, I can today.” Cas’ voice was slow, but his words seemed calculated.

“That would be awesome. Thanks, man. How about the library?” When Cas nodded, Dean clapped his hands together. “Perfect. I’m gonna let my brother know to stick around today, so I may not get there right away, but worst case, give me five minutes.”

Something changed in Cas’ gaze, but Dean couldn’t tell what it was. Some new kind of stress? Maybe a level of calm instead? Either way, Dean watched as Cas offered his gentle smile again and nodded his head.

When the bell rang, the sound of sliding desks, shuffling feet, and loud voices filled the air. Dean shot Cas one final wave over his shoulder as he called, “See ya after school,” and then joined the throng of students in the hallway.

_ Staying after school to work in LMC. Meet me there. _

From his desk, Dean sent his brother a text. He knew that Sammy didn’t check his phone much during the school day, but was hoping he’d get it before three o’clock so Dean didn’t have to hunt for his little brother before meeting in the library. Thankfully, it didn’t take long before he felt his phone give a small buzz. Checking quick, he saw the thumbs up that Sam had sent, and then he tucked his phone away again.

“Alright, everybody. Happy Tuesday! Let’s get started.” Mrs. Milton pulled the classroom door shut as she turned to face the class.

When the final bell rang, Dean made his way down to the library. It had been easy to go to his locker before eighth hour started and grab what he’d need for after school. Since the weather outside was still gorgeous, he had also taken his leather jacket to his last class with him, saving him time before having to meet Cas.

As he approached the doors, he noted the clock on the wall: 3:00. Smiling to himself, he walked into the large room, searching for that newly familiar face. When it looked as though he hadn’t arrived yet, Dean found a table against the back bookshelves and dropped his stuff to the floor beside him. It wasn’t surprising that he’d gotten there first; the library was not far away from his pre-calc class.

Dean was digging through his backpack, taking out his textbook and notebook when he heard hurried whispers coming from the bookshelves behind him. He glanced around him briefly, but didn’t see who the voices belonged to. Resolving to focus on his own business, he was flipping through his notebook to find the earliest stuff for APUSH that had confused him when he realized that the voice he’d heard was Cas’.

His interest now peaked, he turned his head slightly to listen.

Cas’ voice was a whisper, although it seemed loud and slightly exasperated. “Damn it, Charlie, I don’t know what to do!”

“Okay, okay, just chill,” another voice replied. “Just--I don’t know, keep it together, dude!”

Cas made a sound as though he were choking on his spit. “What the f-- What do you mean ‘keep it together’? I just told you, I’ve done nothing but make a fool of myself all day. Like, I haven’t been able to spit out a coherent thought and I just fuckin’ stare at his lips all the time! I’m an idiot! Why would I agree to help him with this stuff? I could have said no!” His voice was rushed and frantic, and in the short silence that followed his words, Dean started wondering if he should find a way to call this whole thing off. Although he needed help on this early American history stuff, the last thing he wanted to do was be a dick to the poor guy.

Whoever Cas had been talking to--Charlie somebody--responded bluntly. “You could have, and maybe should have, but ya didn’t, Cas.” After a moment, Charlie spoke again, and this time her tone was kind and gentle. “Castiel, you need to cut yourself some slack, alright? So you have a crush on the guy. Big whoop. And so what if he knows it. You think straight people don’t coexist with people they have crushes on too? You really think that their crushes don’t know?” She let her words sink in.

“But, Charlie,” Cas began again. Even though Dean couldn’t see him, he was imagining Cas’ pale, worried face. “Maybe that  _ is _ what straight people do, but I’m not straight, and people are gonna talk and I don’t want him resenting me. Like, it was one thing where he didn’t know that I existed, but now that he  _ does _ , people could start saying shit, Charlie, and then--”

“Hey, Dean.” A jolt of surprise ran through him as his little brother dropped himself on the chair across from him. Sam had just started to open his backpack and dig out his own textbooks and stuff when Dean turned his head and saw two  _ very _ startled faces peering at him over the top of the bookshelf. Just as quickly as he saw them, Cas and the fiery redhead with him disappeared, and he turned back to his brother.

“Hiya, Sammy. I’m meeting somebody to work on APUSH.” Dean found that he was feeling a little uneasy, so his voice lacked its typical confidence; Sam didn’t seem to notice, and instead chatted away cheerily.

“Is that what you had to get here early this morning to figure out?” Dean nodded in response, and Sam stood up. “Well, this works out well for me because I have stuff to do, too. I’m gonna hop on one of the computers to work on my science project. Just let me know when you’re almost done.” Without waiting for a response, Sam collected the materials that he needed, tucked his backpack under Dean’s table, and pushed in his chair before walking towards the cluster of desktop computers by the library entrance. Dean was watching him settle into his seat when he saw a head of red hair sprint out the library doors.

From his peripheral, Dean saw movement. Turning, his eyes locked onto Cas. The other boy was standing a couple feet away, very clearly horrified; Dean could see the quickness of his breathing as his chest rose and fell in rapid bursts.

At that moment, Dean closed his textbook and notebook, stacking them and pushing them off to the side. When he turned his attention back to Cas, he found that he hadn’t moved, but Dean could now see that his eyelids looked dewy and he was fidgeting with his hands at his sides.

“Hey, Cas.” Dean rested his arms on the table in front of him, not breaking eye contact. “Wanna sit down?” When he didn’t move, though, Dean gestured to the seat across from him that his brother had vacated. Although it took a moment, Dean’s gaze remained locked on Cas’ until eventually, he took the seat indicated for him.

The silence that fell between them was loud, but Dean didn’t know how or where to start. He knew that Cas wasn’t going to talk, though, so giving a sigh, he leaned forward across the table. “Cas, I don’t think we should do any history stuff today.” Cas broke eye contact as his eyes dropped to the table between them. His face was devoid of expression, and yet there was a sadness about him. “I think we should talk a little bit, and then maybe try APUSH stuff another time if that works out.”

Cas tentatively lifted his eyes from the table, his eyebrows constricting slightly in confusion, but he didn’t speak.

“Alright, so, I wanna say some stuff, and you don’t have to say anything back if you don’t wanna, but either way, I think we need to clear some things up.” Dean didn’t wait for Cas to respond (he wasn’t sure the kid would even if he could at that point).

“First off, I totally wasn’t trying to listen in on you guys. I got down here right away, and just figured this table was easy and within eyesight from the doorway. I didn’t think you were here yet, so I wanted to make sure you’d see me when you walked in.

“Second, if you don’t wanna do this, Cas, I told you that it was alright. Like, seriously. Zero hard feelings, I promise.”

Once again, Dean watched as Cas perked up slightly as though preparing to speak, but then closed his mouth once more, pushing up his glasses with a trembling hand instead.

“Alright, we’ll come back to that. I’ma keep going.” And so he did. “Dude, you have a crush on me.” Cas’ pale face flooded with red as he cringed. “Hey, Cas, that’s not an issue. Your friend Charlie was right. You really think I’ve never had a crush on somebody where they’ve  _ known _ it too?”

Cas’ eyes were closed tightly and Dean could see the tension that seemed to prevail through him. “Dean.” His voice was quiet, but as he spoke, his eyes never opened. “This isn’t the same, though. A lot of people don’t take kindly to--people like me.” The final three words seemed to rob him of his dignity, and as Dean heard them, his heart dropped.

“You got me there, man. I mean, you’re right. Some people are total douchebags, but I just hope that you realize that not everybody’s like that.” Dean stopped briefly. He knew that Cas was listening even though his eyes remained hidden; Dean could see a few small tears trickle down his cheeks. “This isn’t my business, so feel free to tell me to fuck off, but does your family know?” At this, Cas took a quick breath, but offered a nod. “And?”

When he spoke, Cas’ deep voice was uncharacteristically high, and although he hiccupped and stuttered through his words, he never opened his eyes. “Uhm, m-my one brother Gabe has been nothing but wonderful about it. He and I have always been su-super close, so I th-think he maybe even knew before I was r-ready to admit it to anyone, let alone myself.” At this point, Cas’ blue eyes were visible, but surrounded by fresh tears. His voice was still meek and he wouldn’t look Dean in the eyes, but him simply speaking was a good start. “Once I told Luke, he was really good about it, too. And Michael--” At this, silent sobs began to shake through him more freely than before. “M-Michael has been amazing actually. He-He told me that he loved me and was p-p-proud of me, and he’d never r-really said anything like that to me before.”

“Cas, man, that’s great.” Dean’s voice was soft and gentle; although he was not normally one for heart-to-heart conversations with his friends, he was beyond thankful that he could be there for Cas at that moment. But even then, he felt a pang of guilt for having inadvertently caused any of this grief in the first place. If he hadn’t asked Cas to tutor him, none of this would be happening, but Dean had had no clue about Cas’ feelings for him or that their interactions would cause the poor guy this kind of trouble. “And what about your parents?”

Cas remained silent, and for a moment, Dean did as well. As he patiently waited, not wanting to rush Cas any more than he already had, he noticed the body language of the boy in front of him. Although the lenses of his glasses had become cloudy as he wept, Dean could see Cas’ bright blue eyes stare off into the distance, as though silently reliving a painful memory; he sat in his seat, shoulders hunched forwards as a clear form of self-preservation, and his tightly held hands fidgeted in his lap.

“It’s alright, buddy.” The silence told Dean everything that he needed to know. “I’m glad that you have great brothers. I hope to meet them someday.”

At that comment, Cas lowered his head to the table, allowing it to fall against his forearms and he shook. Fresh sobs--louder now than before--ran through him, and Dean was left confused and panicked. “Whoa, Cas, I’m sorry. I-I don’t know what I said.”

Cas raised his eyes to look at Dean, sniffing loudly before trying to speak. “Dean, I am the epitome of pathetic right now, I have very little to offer, we barely  _ know _ each other, and yet I’ve just dumped upon you the burden of my life! And here you are, listening so patiently and kindly, and then you state that you hope to meet my brothers someday.” With shaking fingers, Cas removed his glasses from his face and tried to wipe at the lenses, but finding it to be too difficult of a process, he threw them aside instead. Bouncing twice along the table, they disappeared off the edge and landed softly on the floor.

Pushing himself from his seat, Dean moved to the chair right next to Cas and put his arm around his shoulder. This action seemed to fluster Cas more as he sputtered nonsense before leaning into Dean’s arm, allowing himself to be held. They remained there for several minutes until Cas’ breathing steadied and he removed his head from Dean’s shoulder.

“Dean, I was listening and therefore know what you said before, so please don’t feel the need to repeat the sentiment, but I do sincerely apologize for all of this today. From the collision and foolish behavior this morning, to the awkwardness of our lunch, and this painful interaction here, I am so terribly sorry, and yet I would like you to know that I am very thankful for your kindness.” The words came out in a steady stream, and Dean couldn’t help but smile even though Cas never moved to look him in the eyes. “If you would still have me, I would be happy to be your tutor. I promise that I am not normally like this--well, that’s not entirely true, but I can assure you that I don’t normally reveal this type of behavior to anyone outside of my friend Charlie, with whom I was speaking before, or my brother Gabe.”

“If you’re up for it, that would be awesome, Cas.” Dean gave him a light pat on the back and Cas allowed himself to smile briefly in response.

“And I would like to add, I promise that I won’t let my feelings for you get in the way of anything here, and if I ever make you feel uncomfortable through my behavior, or if you need to end our tutoring because of, uh, other factors, I completely understand.”

That final comment had Dean slightly perplexed, and although he could have let it go, he chose not to. “I’m not sure what you mean, Cas.” He didn’t know Cas well--fuck, they’d really only met that morning--and yet he also felt like he knew the kid pretty well by now. He’d admitted a lot of personal stuff to Dean that day, so what cryptic thing was that final remark referring to?

Cas shifted uncomfortably, glancing over his shoulder and looking around the library, leading Dean to do the same. The room was fairly full at that point with students either working independently, using the space for collaboration, or simply doing their own thing, and yet nobody seemed to be paying them any real attention. For that, Dean was grateful. So often, people couldn’t keep their noses out of other people’s business, but then didn’t seem to be one of those times.

“I mean, I think it’s inevitable that some members of your social circle take issue with, or possibly even make false accusations regarding, our interactions, and if that is the case, I will be happy to step down as your tutor, or at the very least fulfil my tutoring responsibilities in a more discrete way.”

“Oh, fuck that, Cas.” Dean’s voice was a bit louder than necessary at that point, earning him a scowl from the librarian. Giving Mr. Shurley an apologetic wave, he looked back over at Cas before continuing to speak, this time in a quieter tone. “Dude, first off, I think you’re assuming that my popularity is more of a thing than it actually is; believe me when I say that I’m not all that.” That comment earned a slight blush from Cas, but Dean kept going. “Second, I’m hoping that people at this school aren’t as big of fucks as that, but if you’re concerned about our classmates, then I respect that concern. Third, even  _ if _ spending time with you was going to hurt my ‘reputation’ or make people talk, I don’t fucking care. Life’s too short to care what asshats have to say, and I don’t need that bullshit in my life, and neither do you. I make my own decisions, so you don’t worry about that. And fifth, or whatever fuckin’ number I’m on, you don’t have to change who you are to appease me. Your friend from earlier was right; straight people hang out with or work with their crushes all the time, and this ain’t no different. Now, if  _ I _ make you uncomfortable or you have any concerns with helping me, don’t hesitate to tell me. I’m a big boy; I can handle it.”

Dean watched Cas take a long calming breath before exhaling slowly, and as he did, he smiled and nodded his head slightly. Cas then extended his hand, as though trying to settle something officially, and Dean chuckled as he accepted with a firm grip of his own. Although Cas’ hand was wet--Dean assumed either from sweat, tears, or maybe snot--he didn’t say anything, but instead put an arm around Cas’ shoulder and gave it an affectionate squeeze.

In an instant, Cas’ mood seemed to change as he sat up and began collecting his materials from the table and the floor beside him. It was then that Dean remembered that Cas had chucked his glasses to the floor. Getting off of his own chair, he made quick work of finding them and cleaning them the best he could with a corner of his shirt before handing them back to Cas, who accepted them gratefully. Checking his phone for the time, he read 3:42.  _ Damn, time flies when you’re having heart-to-hearts _ .

“Well, I think this is as good a place as any to stop for the day.” Dean smiled as he grabbed his own things, before reaching beneath the table and taking his brother’s backpack. “How are you getting home, Cas?”

Cas had retrieved a tissue from somewhere and was trying to clean himself up when he paused. “Uhm, I didn’t really think that far ahead, to tell you the truth. I was a little scatterbrained today and I typically get a ride from Charlie, but I only live a couple miles away and could probably use the fresh air.”

“Nah, I’ll give you a ride.”

“Oh, really, Dean, I appreciate that, but I will walk.”

“Dude, it’s the least I can do for you sticking around to help me.”

Cas gave a shy smile. “Well, we spent the entire time talking about me and my problems, so if anything, we stuck around to help  _ me _ .”

“Don’t care. Come on, Cas. I just gotta drag Sammy off the computer. He’s probably looking at porn.” Dean had a habit of laughing--or at least smiling--at his own jokes, and this was no different, but adding Cas’ mild look of horror just made it all that much better for him. “Come on, Samantha, time to pack up.”

Offering a dramatic roll of the eyes and tilt of the head, Sam began to save his work and shut down his computer. “You know, Dean, you make it almost impossible for me to tell people that we’re related.”

“Not just related, Sammy. You’re my teenie, weenie baby brother who I just couldn’t live without!” His tone and words were dripping with sarcasm, and yet the sentiment was true beyond anything else: Sam was the most important person in Dean’s life, and Sam knew that, too. When it came to showing love and affection, neither of them did that real great with one another unless it was something pretty major, but neither brother ever doubted it for a second. “Oh, Sammy, this is Cas. Cas, this is my brother Sam. We’re gonna give Cas a ride home today.”

Although Cas’ face was a total mess and Dean knew that it was very obvious that he’d just been sitting at a back table crying his eyes out for the past half an hour, his beautiful oaf of a brother never said a word, and he loved him all the more for that. “Good to meet you, Cas. Dean was telling me before that you drew the short straw and have to help him out with history. Good luck.” That brought a smile to Cas’ face.

“Oh, I’m happy to do it. I enjoy helping people when I can and your brother is a real treat.” Seeming to regret his choice of words, Cas’ face grew pale as he looked between Sam and Dean, clearly waiting for some kind of verbal response, or maybe even physical retaliation.

“Oh, Cas, you poor, poor soul. You’ll learn soon enough that my big brother isn’t really sweet, but more like a cavity that just throbs and brings you nothing but discomfort.”

Dean feigned shock. “Ouch, Sammy. That hurt. And just  _ for _ that, you get the back seat.” A look of confusion and regret appeared across Sam’s face, but the damage had been done. Dean let his little brother’s backpack fall to the floor as he grabbed Cas by the arm and led him out to the parking lot with Sam yelling behind them.


	5. Million Dollar Question

**Summary for the Chapter:**

> After the day he had, Cas needs to process everything that happened. In the end and with the help of two of his favorite people, he's left weighing some pretty hefty options.

On a day like the one he had, he was beyond thankful that Gabe was the only sibling still living at home and that his parents were frequently absent themselves.

His departure from the Winchester car had been both a relief and a disappointment. Although he was thankful that he could collapse onto his bed and cry as much as he wanted, the idea that he had just spent much of the day, in one way or another, with  _ Dean Winchester _ had him feeling drunk and high (in all fairness, Cas had never been either, but he figured the overall icky feeling and level of lightheadedness that he was experiencing were comparable).

By the time they pulled up outside the Novak residence, Cas had learned that Dean and Sam lived a street over. “Told ya that taking you home would be no problem,” Dean said with a smile. The sight of Dean’s sparkling green eyes and toothy smile ripped through Cas, no matter how hard he tried to keep those feelings tucked away.

Cas got out of the car, leaving the door ajar for Sam to claim the spot beside Dean. “Thank you once again for the ride, Dean. And for, uh, everything.” He felt his cheeks grow hot; the idea of Sam knowing what had transpired that day was nauseating to consider, but with puffy eyes and blotchy skin like he had after his disastrous and weepy afternoon, he knew that it was inevitable. “Sam, it was a pleasure meeting you. Have a wonderful evening.”

As the shiny black car pulled away from the curb, Dean called out the window, “Hey, tomorrow in the LMC after school?”

Although he fought the feeling with everything that he could muster, a sense of elation filled his chest as he smiled, nodded, and waved goodbye. The car was just turning the corner in the direction of the Winchester home when Cas heard the front door of the house being thrown open. He turned around just in time for two pairs of arms to be wrapped around him.

“Aww, Cas, I am so sorry!” Charlie sounded near tears. When he turned his head towards her, allowing her to see his physical condition, she actually did gasp. “Cas, who did this to you? Did  _ he _ do it? Did he hurt you?”

The second pair of arms released his waist as Gabe grabbed both sides of his face and spun Cas to look at him. In an instant, he could see the tension build in his brother; although he was of short stature, standing no taller than five-and-a-half feet tall on a good day, he seemed menacing in that moment. Before he could do more than glower and clench his fists, however, Cas interjected.

“Nobody hurt me.” Both Charlie and Gabe seemed to distrust this statement as they shared a concerned glance before returning their eyes to his mess of a face. “To say that today has been an emotional clusterfuck of a day would be an understatement. Believe it or not, what you see here was, more or less, self-inflicted.” Reading the looks of disbelief still plastered across their faces, Cas allowed a heavy sigh to fall from his lips. “Let’s go inside. I need several ibuprofen, but then I’ll tell you all about it.”

“Charlie got me caught up on everything that happened until the library. That’s where we were when we saw that atrocious  _ thing _ pull up outside the house.” In true Gabriel fashion, he was set on blaming, and even hating, Dean for the stress that his brother had experienced, and thus far, nothing Cas said had been able to change that.

“Oh, good.” Cas was not going to hide the passive-aggressive feelings building within him, and with the day he had, he decided to let them show. “Then you realize that  _ I _ ran into him in the hallway,  _ I _ froze like a fool when he helped me before school started, and he visited  _ me _ for lunch and proceeded to patiently walk through my anxieties with me.” These words seemed to confuse his brother; Gabe wanted so badly to hate  _ someone _ for how Cas was feeling, and yet Dean had truly done nothing to deserve his hatred.

The three of them had moved into the comfort of Cas’ room and were all crowded together on his bed. Their parents were not going to be home for several days--one of the benefits of their shared and never-ending book tours--but even with the house empty, it still felt right to have this personal conversation in a safe, personal space.

“Cassie, I feel like we need to address the elephant in the room here: you don’t need anybody’s validation, capice? It’s all well and good that Mr. White Knight Winchester was there for you,”--at that point, Gabe rolled his eyes dramatically--“but it doesn’t matter what he says or thinks; you have nothing to be ashamed of.”

Dean’s words came flooding back to him at that moment, and he couldn’t help but smile.

“Dude, I’m not even trying to be funny now!” Gabe was clearly offended by Cas’ amused expression, so he felt it best to elaborate.

“‘Life’s too short to care what asshats have to say.’”

“Exactly, Cas!” Gabe, who had been leaning back against the headboard, was now reaching for Cas’ shoulders, shaking him. “Forget that asshat!”

“No, Gabe,” Cas smiled again, “that’s what Dean told me today.” He watched as the words began to sink in and Gabe sat himself back up. “I--” He was struggling with how to proceed; he didn’t really keep secrets from Charlie or Gabe, so it wasn’t that he had problems talking with them about what happened, but rather admitting the low opinion that he held of himself. “I vocalized to him today that people will likely gossip as a result of our public interactions--you know people--and without hesitation, he told me that he didn’t care, that I shouldn’t change for anyone, and that life is too short to worry.”

Gabe seemed to relax a little at the sentiment, and Cas was left comparing his relationship with his brother to that of Sam and Dean. Although he had only spent a very short time with the Winchesters that day, he felt that Dean’s love for Sam was comparable to Gabe’s love for him. This was something so small, and yet Cas appreciated knowing that such a similarity existed between them.

Soft pressure on his leg brought his attention back to Charlie who had been quiet since he got home. “Cas, tell us what happened after school.” Although she spoke softly and slowly, there was a sense of urgency to her as well.

As he began, he brought Gabe up to speed on the conversation that he and Charlie had been having before they became aware of Dean’s arrival. From there, he jumped into the story, leaving nothing out. He told them everything that Dean had said, starting with his apology and how he hadn’t intended to eavesdrop; how Cas didn’t have to tutor him if he was uncomfortable for any reason; how it wasn’t a big deal for them to still work together knowing about Cas’ crush. He then explained how Dean cared enough to ask about his support system at home; and acknowledged that, although he didn’t think people would take such an issue with his sexuality, Dean was not in the position to know or really understand what Cas was going through. When he was describing the millionth time that Dean had simply sought to console and comfort him that day, he noticed the expressions on the faces around him. These two people, while previously hellbent on revenge against Dean Winchester for whatever harm he had caused their beloved Cas, had visibly softened.

As Cas concluded his story, a silence fell around them, only broken by the slow exhales from both Charlie and Gabe. Neither seemed to know what to say, which was a very rare thing for them both.

“So, like I explained earlier, what you see here was all self-inflicted. The  _ only _ thing that Dean was guilty of was being the subject of my infatuation, and thereby inadvertently sending me into a state of anxiety by simply speaking to me today.”

Again, neither spoke, but simply nodded their heads in response.

“Yeah, you got me there, Cassie,” Gabe remarked as he ran his fingers through his own brown hair. “What are you gonna do?”

But before Cas had a chance to respond, Charlie perked up. “Well, it’s obvious, isn’t it?” Seeing that neither Cas nor Gabe were following, she continued. “He’s got to weigh some options here. Cas, you’ve laid all your cards on the table. Dean is well aware of where you stand, and he’s made it clear that he’s got no problems with you  _ for you _ . So, as I see it then, you have two choices. You can either accept the fact that you’re never going to stop crushing on this guy, be his tutor, and actually form some kind of relationship with him knowing that this is your senior year and you may never see one another after graduation, or else cut your losses here and now. Make a clean break and walk away without getting too attached, and having to worry about the disappointment later.”

“Well, holy fuck, Charlie. How friggin’ obvious!” Gabe’s words were dripping with sarcasm as he leered across the bed. “I mean, when you put it  _ that _ way, then it is so crystal clear what Cas needs to do!”

Shaking her head, strands of red hair fell across her face, clearly unamused by Gabe’s attempts at humor; Cas had never been a popular person, but he was beyond thankful that both his brother and Charlie were fixtures in his day-to-day life, and that they got along so well with one another. Their playful banter always lessened Cas’ anxiety, and although he wasn’t sure if they knew that, it was nonetheless appreciated.

“She does have a point, little bro. Those do seem like the two best options. What do you think you’re gonna do?”

_ And that, ladies and gentlemen, is the million dollar question. _


	6. The Tardy Tutor

**Summary for the Chapter:**

> Dean and Cas have their first real tutoring session and make plans to get together outside of school.

It was five minutes after three and Dean was sitting at the back table of the library once again. Sam had already dropped off his backpack and gone to claim a desktop to work on some science project, and Dean was left waiting for Cas. Although he had seen him briefly that morning, he didn’t see him at lunch and he wasn’t in history. It would have been helpful if he’d gotten his phone number to see if they were still supposed to meet, but you know what they say about hindsight? It’s 20-20 and all that shit.

Several more minutes went by, and yet nothing. Dean was just about to call it a day when he heard rushed footsteps. “Dean!” A voice echoed through the otherwise silent library. Looking up, he saw a very winded Cas sprinting towards his table, his heavy backpack bobbing up and down with each step. The sight was truly something and Dean was left processing.

“Dean!” Cas gasped as he collapsed onto the seat across from him. At that moment, Dean became aware of several things: first, Cas clearly didn’t run often; and second, nobody else in the library seemed to know what the fuck was going on, either, but everyone was watching intently. “I’m so...sorry.” Cas’ shoulders rose and fell dramatically as he sucked in air, trying hard to catch his breath.

“Cas, relax. Just breathe for a minute.” Seeing as Cas had his head down on the table as he worked to get his breathing under control, Dean glanced around the room. It looked as though every eye was on him, and when he saw Sam’s curious expression, he simply shrugged in response. Everyone seemed to accept that as an answer because work and quiet conversations began once again.

“Truly, Dean.” Cas picked his head up; although his skin was still blotchy and his glasses were fogged, his voice was steadier. “I am very sorry for my tardiness. I left school at the end of third hour and only just returned. My appointments took longer than I had anticipated, and I realized too late that I had no way of communicating this to you.”

“Wait, you came  _ back _ ? Like, you just came back to school for  _ this _ ?”  _ Who the fuck would come back to school if they didn’t have to? _

Dean could only describe the look on Cas’ face as perplexed and offended. “Dean, I gave you my word. And like I said, I had no way of communicating with you, so you could have waited here indefinitely.” He got the answer to his question.  _ Who the fuck would come back to school like this? Cas, that’s who. _

“Hey, man, indefinitely is a bit of an exaggeration.” Dean smiled as Cas seemed to shrink back slightly. “We graduate in June, so for sure, I’d be gone by then.” This response seemed to calm Cas as he smiled.

“So,” Cas began as he removed his APUSH materials from his backpack, “let’s try this whole tutoring business again. A.P. U.S. History. Where would you like to begin, Dean?”

With a grin, Dean flipped through the beginning pages of his notebook.

By 3:55, most of the library had emptied, leaving only them, Sam, and the librarian. While the after-school hours for the library technically ended at 3:45, Mr. Shurley had let them know that they could keep working and he’d give them a heads up when he was almost done.

“Cas, straight up, I think I’m actually getting this.” Dean sat back in his seat and felt a small weight lift from his shoulders. Although the A.P. test was still months away, he had been a bit worried about not getting the college credit in the end if he bombed the test.

“Well done, Dean.” Cas was pushing up his glasses as he smiled across the table. “We’re off to a great start.”

That brought Dean a laugh. “Yeah, a  _ start _ . We just spent the last 45 minutes going over the first page of notes. At this rate, we may get through everything by next summer!” Although he was being sarcastic, he was still a little discouraged that they had only gotten through such a small portion of material in their time.

“That might be true  _ if _ you were needing help with  _ all _ of the material, from start to finish; however, you said it yourself: you struggle the most with early American history. That will take us through first semester only, and it just serves as more review and refresher of that older material as we get closer to the test.”

“Dude, I knew you were smart. I like the way you think.” The compliment made Cas blush, but he still maintained eye contact. “Does this mean you’re willing to keep tutoring me?”

“Oh, absolutely. Like I said, I gave you my word. And as long as us working together doesn’t make you uncomfortable and your schedule continues to permit it, I would love to do so.” In that moment, Dean began to consider what he knew about Cas. The kid had a crush on him--from what he saw the day before, it was a doozy of a crush, too--and while he was clearly struggling with a lot of insecurities, he was there, tutoring Dean despite it all. When and if the time would ever be right, he resolved to tell Cas that he really appreciated how he was putting himself out there to help him, but for the time being, Dean thought it best to stay away from any more conversations that were too personal.

“Rock on,” Dean smirked. “But seriously, don’t  _ ever _ make a special trip back to school again for this. Like, there’s nothing that can’t wait until later.” This made Cas smile and Dean noticed that his eyes twinkled when he did.

“Hey, guys.” Mr. Shurley was leaning over the circle desk, grinning pleasantly at them. “I already talked to your brother, but I just wanted to let you know that I’ll be ready to head out in about five minutes.” Dean and Cas both smiled in response, and Dean watched as the librarian seemed to drop down several inches as he turned away.  _ Dude had to stand on a box to see us over the counter _ . Dean found this thought to be very amusing.

Just then, Dean had an idea. He reached his hand across the table, and although it took a moment before Cas noticed, he eventually did, but was left clearly perplexed. “Lemme see your phone.”

Cas’ eyes grew as he slowly reached into the side pocket of his backpack and pulled out an outdated flip phone. “Dude, for real?” Dean asked, turning the phone over in his hands. “You use  _ this _ ?”

“That was one of the reasons I was gone today.” The blush in Cas’ cheeks seemed to be spreading to his ears and down his neck, both of which were glowing bright. “Both my phone and my glasses broke last night, and Gabe picked me up today to get them both addressed. This is Michael’s old phone, but I’m using it until my new one comes in.”

“I’m just messin’ with you, Cas.” Although it took him a moment, Dean found the contact list and added himself before handing the phone back across the table. “If we set up a time to meet, but you can’t, just shoot me a text and let me know.”

Cas nodded slowly, not taking his large eyes off of Dean.

“Yo, Sammy, you almost ready over there?” Dean’s deep voice called out, making Cas jump slightly. As Dean peeked to look at his brother, Sam gave a thumbs up as he started collecting his things. “Cas, you good with a ride again?”

“If you really don’t mind, that would be great.”

“Hey, man, I wouldn’t have asked if I minded.”

“And I appreciate it, truly, but I do plan on making some arrangements for myself. My friend Charlie has offered to come back when and if I need her to, and Gabe is typically available, but Wednesdays, he tries his hand at stand-up comedy, so he’s unavailable this evening.”

“Stand-up, huh? He any good?”

Cas smirked as he rolled his eyes; it was one of the most genuine and unabashed responses Dean had seen from him. “You know, his type of humor isn’t necessarily  _ my _ type of humor, but people do seem to enjoy him.” The smile that was etched across his face made Dean think that Cas had witnessed his brother’s routine in-person; Dean knew the look of a proud sibling when he saw it.

“Well, good on him. Depending on where it is, maybe I’ll have to check it out sometime.”

“It’s at a local tavern called The Roadhouse. It’s not a big place, but they have a small stage and the audience seems friendly enough.”

“The fuckin’ Roadhouse? Dude, that’s my mom’s place!” Cas’ face went blank. “Well, not my  _ mom _ mom, but she’s taken care of us ever since we were kids.” At that moment, Sam was coming back to the table and Dean couldn’t contain his enthusiasm. “Sammy, Cas’ brother does stand-up at The Roadhouse tonight. What do you say we go and watch and get some dinner?”

Sam offered an impartial shrug, leaving Dean to question why he ever bothered to ask his brother, the killjoy, anything.

“What do you say, Cas? Wanna join, or are your folks expecting you home soon?” Looking back at Cas, the guy seemed at odds with himself. Biting his lip, he said softly, “My parents are out of town until this upcoming weekend, so besides Gabe, there’s no one at home.”

“Then it’s settled!” Dean called triumphantly. Throwing his stuff in his bag, he started briskly walking towards the door with Cas and Sam following briskly. “Thanks again, Mr. Shurley!” he called as he stepped out into the hallway. Although he heard a response, he had no clue what was said, but he made his way to the parking lot all the same.


	7. The Roadhouse

**Summary for the Chapter:**

> The three boys go to The Roadhouse, enjoying the atmosphere, the food, and some real heart-to-heart.

**Notes for the Chapter:**

> Even more than the others, this chapter really looks at insecurities, anxieties, and self-esteem issues. A big thing about this whole story is a person's struggle to love and accept themselves, and we've really seen that from Cas so far. I can assure you that the entire story won't focus on these inner conflicts, but because I think these are things that many of us struggle with (whether that be on a small-scale or large-scale), I wanted to take the time to really address them. I also think it's important that people find support systems that work for them, even though that doesn't make those feelings disappear in an instant. That's why so much of the story up until this point has dealt with real heart-to-heart conversations between Cas and Dean: together, they're trying to work through some of these internal struggles.
> 
> Thanks for your patience as we get to know the inner-workings of these characters before we do more with exploring their interpersonal relationships.

The Roadhouse was an older rustic bar in an underdeveloped part of town. Dean explained that their mom had opened the place before she and Bobby adopted the boys well over a decade before, so Sam and Dean grew up with The Roadhouse as their second home. Sitting in the front seat of the Impala, Cas watched Dean closely as he shared some fond childhood memories that were held within that building. With each story, he saw Dean’s vivid green eyes sparkle with nostalgia, and although Cas had never been inside the place, he felt as though he had lived each moment with them.

Upon their arrival, Cas noted that the exterior of the building had a certain rugged charm, even with the lopsided awning that ran along the roof and the outdated front porch that seemed likely to crumble under too much heavy foot traffic. As they pulled into the unpaved parking lot, however, Cas was surprised by the number of cars; for it being a Wednesday evening, the establishment seemed surprisingly busy.

Driving through the lot, Cas could hear loud music and laughter coming from the front entrance. The song that was playing sounded very familiar, and he was listening intently to see if he could identify the title, when he realized that Dean was driving past several empty parking spots as he rounded the corner of the building. Seeming to understand Cas’ confusion, Dean informed him that Ellen preferred her boys use the service entrance in the rear; she liked being able to keep an eye on them as they came and went. Although Dean said this with a roll of the eyes, there was a smile on his face, and Cas found it all to be quite endearing.

Dean turned off the car and removed the key which he dropped into the pocket of his leather jacket before turning to face Cas in the passenger seat. In that instant, Cas felt a strange sensation in his stomach, but he wasn’t sure where it came from. “Well, should we do this?” A cocky grin was stretching across Dean’s face, and Cas felt a swarm of butterflies erupt within him.

Staring into the depths of those gorgeous green eyes, Cas again found himself at a loss for words, so he offered a small smile and nod in return. This made Dean chuckle, and as he gave Cas’ arm a playful punch, he opened his door and stepped out.

Before Cas was able to do the same, he felt a soft hand on his shoulder. The gentle contact gave him a start as he had forgotten that Sam was in the backseat.

Turning his head, he looked into Sam’s hazel eyes. “I’m glad you came out with us tonight, Castiel.” Cas immediately noted Sam’s sincerity, although he was not sure what inspired the comment. With Sam and Dean seeming to have such a close relationship, he assumed that Dean had shared much, if not all, of their previous conversations with Sam, but the idea that  _ both _ Winchester boys knew how pathetic he was left him feeling queasy. Was it possible then that their mom would also know all about him? If so, was it really smart to be going into a building full of drunks, where anybody and everybody could know his life story?

He could hear Sam opening the back door and climbing out of the car, but Cas remained, still deep in thought. He was contemplating asking to go home when the sound of something heavy hitting the roof of the car made him jump. Looking out his window, he saw Dean’s smiling face peek down at him, his one arm placed on top of the car as the other hand pulled open the passenger door. “You alright there, Cas?”

Cas felt as though he could crumble in his seat as he looked at that beautiful smile, and the knowledge that the smile was meant for  _ him _ was almost too much. Not 36 hours before, he and Dean had been complete strangers, and yet there he was,  _ sitting in Dean’s car _ , about to go to dinner with him and his younger brother while watching Gabe do stand-up comedy. He wasn’t sure if the universe was cruel or something to be grateful for, but he was hoping for the latter.

Although he could feel his heart thumping violently and his hands were trembling in his lap, he tried his best to appear calm; as Dean pulled open his door, Cas made quick work of getting out, rubbing his hands on his pants in the hopes of steadying himself.

“Alright, fellas. Let’s do this.” Dean slammed the door shut before throwing an arm around his neck and Sam’s, and together, they made their way to the back entrance of The Roadhouse.

Sam pulled the handle and pushed the heavy steel door open for the three of them to walk inside; although he was the youngest and only a freshman, Sam was already the tallest, and from what Cas could see, he was nowhere done growing yet.

Upon entering the building, the music and voices were once again amplified, and it took a moment for Cas’ eyes to adjust; although setting, the November sun had still been blinding, and the dim lighting inside left him momentarily unable to see. As he blinked, however, he found that his surroundings were coming more into focus. Looking around him, Cas could see a busy kitchen off to his right, with several cooks shuffling past one another in a fairly tight space, and on his left, past Dean and Sam, a small office with its door propped open.

“Honey, we’re home!” Dean called as they moved towards the office, his arms still around the other two.

“Well, well, well,” a voice called back. “I didn’t think I’d be seeing you boys here this evening.” The owner of the voice, a dark haired woman whose face and body language screamed “no nonsense,” walked out to meet them. “How was school?” At this, Dean finally dropped his arms from their shoulders; the absence of his warmth made Cas shiver.

“Eh, you know,” Sam said, leaning down and kissing her on the cheek as she wrapped her arms around him.

“You been working on that science project of yours?” the woman asked of Sam as she turned to kiss Dean’s cheek.

“I spent yesterday and today in the library working on it while Dean got help with his history. It’s not due until next Friday, but I’d say I’m about half done.” Cas could hear the pride in Sam’s voice; although he didn’t know him well, it was clear that Sam took his education seriously.

“That’s my boy!” the woman replied. As she spoke, Cas noted that her voice had a sharpness to it that was intimidating, but her eyes told a different story; they showed a softness that could otherwise be easy to miss.

Dean fired a playful insult at his brother that he covered with a poorly crafted cough, and Sam smiled and shoved at his shoulder. Cas appreciated being able to witness these little moments between them both; he had been marveling at Dean for years, and seeing that he was not just gorgeous, but also kind and funny made his crush seem all the more justified.

“Oh, Ellen,” Dean said as he put an arm back around Cas’ shoulders once again and pulled him back to his side, “this is Cas. He’s the one I was telling you about.”  _ Oh please no _ . The idea that Dean had already told his family about Cas was terrifying; the day prior had been nothing but embarrassing for him, and he cringed at the idea that so many people seemed to know what a fool he had been.

Ellen’s lips quirked as she raised an eyebrow suspiciously. “Oh, yeah. Cas the tutor.” Her voice gave away nothing, and Cas was left unsure of where he stood. As he watched her shake her head slowly, a feeling of fear began creeping through him. “My Dean over here tells me that you’re looking out for him.” What did that mean? Did she know about his crush? Or more appropriately, about his obsession with Dean? “Boy, if he does well on that A.P. test in the spring, I’m tellin’ you now, I’m gonna take you out for dinner.”

Cas didn’t realize that he had been holding his breath, but upon understanding Ellen’s words, he found himself exhaling heavily. Turning to his side, he saw both Sam and Dean giving him a smile, and Ellen chuckled.

“Yeah, you were right about him. He does seem jittery as hell. Relax, Cas.” Ellen patted his upper arm as he felt his eyes bulge. Dean  _ had _ told his family about him, and for the millionth time in the last day and a half, Cas was mortified and wished he could just disappear. “You’re in The Roadhouse, hon. This is a place for good times and lettin’ your worries go, at least for a little while.” Ellen’s features were still intimidating and sharp enough to cut glass, but he allowed himself to smile slightly in response to her words. “There ya go!” This brought a bigger smile to her face as the crow’s feet near her dark eyes became more visible.

“Cas’ brother is taking the stage tonight, so we thought we’d come and watch.”

“Is that so?” Ellen seemed deep in thought for a moment. “Hold on now. Is he a short little guy, about your age, longer brown hair that he keeps swept back, and a shit-eatin’ grin?” All sets of eyes were looking at Cas who nodded at the fairly accurate description of his brother. “Oh, you fellas just missed him, but  _ damn _ , he was good. He’s been here before. I normally sit back here during the open mic, but each week now I’ve had to come out front to see what has everybody in fits. He’s definitely been the fan favorite.”

For that moment, all of his insecurities and concerns vanished. Hearing someone sing praise about his brother left Cas feeling warm and full. Throughout much of their childhood, Gabe had been told that his style of humor wasn’t very funny and would just get him in trouble. Some teachers and kids at school seemed to find him amusing, but those were few and far between, so this unprompted compliment was wonderful to hear.

“Damn, that sucks.” Glancing over at Dean, Cas noticed that he seemed genuinely disappointed, but the disappointment faded as he quickly shrugged. “Well, either way, we’re gonna grab something to eat. I guess this just means that we gotta come back next week, too!”

The idea of spending another evening  _ socializing _ with Dean Winchester had only just begun to sink in when he felt himself being escorted down the hall. He had enough time to glance over his shoulder and say goodbye to Ellen as she waved a hand and disappeared back into the office.

The boys had found an empty table towards the front of the bar, just beneath a bright neon OPEN sign that lit up the window. Although it was the farthest from the microphone and the small stage area, the room itself wasn’t very big, so they were able to see and hear everything even from the distance.

Cas was settling into the booth seat with Dean and Sam sitting together on the other side when a waiter approached their table. In his hands were two glasses which he set in front of the brothers.

“Hey, Doctor Badass!” Dean called with a smile. He and the--doctor?--shook hands before Sam offered a hand and did the same. The man was wearing an interesting and clearly homemade sleeveless plaid shirt, and was sporting the most impressive mullet that Cas had ever seen in person.

“Sam, Dean!” The man’s voice interested Cas; although he was clearly glad to see them, there was a level of monotone that was consistently present in everything that he said. “How’re we doing this fine, fine evening?”

Dean pulled one of the drinks towards himself, rubbing his hands along the side of the glass as he spoke. “Not too shabby. Sammy and I wanted to introduce our friend Cas here to The Roadhouse; his brother had a gig tonight, but Ma said that we missed him. Cas, this fella’s name is Ash, also known as Dr. Badass or Mr. Owes-Me-Twenty-Bucks.”

Ash offered Cas a finger gun salute before turning back towards Dean, his face contorted into a look of slight disbelief. “Yeah, I don’t think you’re remembering that right.” Dean just rolled his eyes in response as Ash turned again to face Cas. “Alright, what can I get you to drink?”

“Just a water for me please,” Cas replied.

Once more with the finger guns and then Ash was gone.

Cas took the opportunity to take in his surroundings more completely. While the bar area wasn’t big, only offering enough room for a single bartender to work comfortably, it made room for a couple dozen booths and tables. Similar to the outside of the building, the interior had an aged and rustic look with its faded concrete walls, old wooden tables, and the mismatched seats available for patrons. Throughout the space, the lighting was very minimal, save for the small area in the back, right next to the hallway that led to the kitchen and Ellen’s office, which was illuminated and supporting a raised stage, microphone, and two large speakers on either side.

“Here ya go, Cas man.” He turned as Ash slid a glass of water in front of him. “You want another one, Dean?”

Dean offered Ash his empty glass and threw a wave of thanks. He then turned towards Cas whose face was unintentionally showing the mild horror that he was feeling. A look of confusion crept across Dean’s face. “What?” He raised an eyebrow in a way that reminded Cas so much of the look that Ellen had given him.

“Did you just inhale a full glass of Mountain Dew?”

“Dude, judgy much?” Dean and Cas shared a smile as Ash returned with another full glass of soda.

“So, folks, what’ll we be having?”

Dean spoke first. “I’m gonna do a double burger, no pink, with cheddar, mayo, barbeque, and a shit ton of fried onions, and a thing of fries.”

“And I’m gonna do a grilled chicken sandwich with lettuce, tomato, and pickles, with a side salad and a light dressing.”

Ash gave them both a nod of understanding and then turned his attention back to Cas. He hadn’t seen a menu and hadn’t thought to ask what his options were, so his brain went blank and he felt slightly frantic.

“Cas, do you eat meat?”

Sam was leaning across the table towards him, his arms crossed casually along the wooden surface.

“Uhm, yes.”

“Okay.” Turning back to Ash, Sam stated, “He’ll do a double burger, no pink, with cheddar, and then everything. And a basket of cheese curds on the side.”

“Rock on, gentlemen. I’ll have that out as quick as they have it made.” With that, Ash was once again gone.

“He didn’t repeat anything back or write any of that down.” Cas was speaking more to himself than to anyone else, but both Sam and Dean chuckled.

“Yeah, the dude’s a fuckin’ genius. He could be doing anything with his life--like, he’s damn near a tech god with a photographic memory--but he’s said he can’t imagine himself anywhere but here.”

Over the next hour, the boys sat at their table, eating, listening to some performers at the open mic, and just talking. Towards the end, Cas had nearly forgotten that he ever had anything to be mortified about. Yeah, his heart still went aflutter any time that Dean smiled at him, but the entire interaction felt so familiar and comfortable.

Their conversation drifted from school and friends to their upcoming homecoming, and Cas shared how excited he was to be playing with the band at half time.

“I really enjoy pep band and performing during sporting events.”

As he drained his soda, Sam wiped his mouth with his hand. “What kind of songs?”

“You mean my favorites?” Sam nodded. “Boy, that’s a hard one.” Cas took a moment to think; there really were so many to choose from. “I really like the song ‘Get Ready for This’; it’s very fun to play on the saxophone. But then I also enjoy ‘Hey! Baby’ and ‘Louie Louie.’ I’d say they are more of your traditional pep band songs, but there’s a reason they are, you know? They’re just fun.”

Dean picked a cheese curd off of Cas’ plate before speaking. “Do you guys have a theme for the halftime show?”

Cas nodded. “Our theme is Cinematic Escape.” He rolled his eyes and smiled. “It sounds cheesy. Essentially, we do two separate movie montage pieces, but being a bit of a geek, I really enjoy a few of the songs in one of them.”

There was a pause before Dean leaned forward, waving his hands in Cas’ direction. “What, are you not going to tell us what they are?”

Cas laughed. “Sorry. Uhm, the song that I really like has part of the  _ Harry Potter _ theme song, a piece from  _ The Lord of the Rings _ , and then the opening from  _ Game of Thrones _ .”

“Shit yes!” Dean's eyes got big and as he smiled, chewed cheese curds threatened to fall from his mouth. “Those titles are awesome!”

“My brother here is quite the high fantasy nerd.”

“Dude, Sammy, back off. Can’t you see the big kids are talking here?” Sam rolled his eyes as Dean smiled and winked at his brother, and then he returned his gaze back towards Cas. “And what about the other piece?”

“Oh, I’m less familiar with those. I know that it has a part of a song from  _ The Godfather _ , and then I think the theme from  _ Indiana Jones _ , and I’m not sure what else.”

Dean dropped his jaw and slammed both palms against the table top, making Cas jump; Sam rolled his eyes. “Oh, fuck. Here we go.”

“Are you telling me that you’ve never seen any of  _ The Godfather _ or  _ Indiana Jones _ ?”

His heart was still pounding in his chest and Cas took a few slow breaths to try and calm himself. “I have heard of them both, and from what I know, each has a sequel, but--”

“A fuckin’ sequel?” Dean was almost yelling and Cas recoiled instinctively, but Sam reached over and placed a reassuring hand on his arm as he smiled. When Dean spoke once again, his voice was just as passionate, but not as loud. “Dude,  _ The Godfather _ has three installments, and there are three kickass  _ Indiana Jones _ movies, too! Your talk of sequels is just blasphemy!”

At this, Cas smiled and his heart rate normalized. “I’m sorry, Dean. I promise to work on this.”

“Hell yes you will!” Again, he smacked the table, but this time Cas was unphased. “How about Friday? You come on over, and the three of us will start getting you caught up.”

_ Oh my god oh my god oh my god oh my _ \--

“Uhm, F--Friday?” His mouth went dry and he felt the need to lick his lips out of necessity. “Friday at y--your house?”

Dean was looking a little concerned. “No big deal. If Friday doesn’t work, let’s pick another day.” He glanced over at his brother. “Far as you know, do we have anything going this weekend?”

Sam’s eyes wandered as he seemed to scour his mental agenda. “Nope, not that I can think of. This is a normal weekend, and then homecoming is next weekend.”

Both boys looked back at Cas, and as they waited silently for his reply, he took a breath and did something that was so uncharacteristic of him: he verbally acknowledged his own awkwardness.

“Can I ask you both something?” He pushed his glasses to the top of his head and rubbed his eyes. When he didn’t hear an audible response, he settled his glasses back on his face, leaned back in his seat, and spoke. “Sam, I’m assuming at this point that, between what you witnessed in the library yesterday and what your brother probably shared with you, you’re aware of my story.” When neither Sam nor Dean spoke, he continued. “I’m the geeky, socially awkward gay kid with no social status, miles of self-doubt, and a debilitating crush on  _ you _ .” He turned his gaze towards Dean and held it firmly. After a few seconds, he dropped his head and felt the dread of anxiety creeping up his throat, but he held it back as he pushed forward. “From everything I’ve ever seen--and Sam, I do realize that I only just met you yesterday--we are as different from one another as possible. You’re both confident, and funny, and popular, and handsome.” While saying that out loud would have typically killed Cas where he sat, it was just one more embarrassing thing in the long line of embarrassing things that he was admitting, so it had very little extra effect. “And I--I’m not that. You both have been so kind to me, but please don’t feel as though there’s any obligation. Dean, no matter what, I’m still happy to help you with your history.”

The laughter, music, and sound of shuffling feet continued to fill the room, but the boys were silent. When that silence was eventually broken, it was Sam that spoke. “So, I’m going to be honest with you, Cas; I hope you don’t mind, but I think what you just said deserves the same kind of honesty in return.” Cas offered a single nod and braced himself. He hated the idea of ruining the relationship that he was forming there, but he didn’t feel right accepting invites out of pity or as a form of compensation for tutoring. When all was said and done, he knew he’d have Charlie and Gabe with him, and that allowed him to hold his head a little higher, metaphorically; in reality, he couldn’t meet their gaze.

The certainty with which Sam previously spoke was gone, and he was left in his seat, seeming to struggle with what to say. Having formulated his ideas well enough, he began again, but each word seemed carefully selected. “You’re right, Cas. I did pick up on a lot yesterday in the library. I couldn’t hear everything, and please believe me when I say that I wasn’t trying to eavesdrop, but between your body language, the occasional words, and the tears, I felt fairly sure with what I thought was going on. After we dropped you off, I asked Dean. Cas, he wasn’t going to tell me  _ anything _ ; actually, he made a point to tell me that several times, but I told him what I had already figured out on my own, and then yeah, he filled in some details because he didn’t want me assuming.”

Cas nodded his head as his shoulder drooped and his gaze fell to the wooden tabletop. Not wanting to look up, he instead focused on the chips and marks that covered the surface, tracing his finger around a water ring left behind from some previous patron. “I’m sorry that he told me anything, Cas, and more importantly, I’m sorry that I asked. It wasn’t my business; I was curious, and yeah, I didn’t know you--I still don’t really know you--but I hated that you were so wrecked.”

Once again, Cas nodded his head, still refusing to look up. “Thank you, but the apology is unnecessary, Sam. I probably would have done the same.” After wiping his hands along his thighs, Cas scooted towards the end of his seat when Sam put a hand on his arm. Looking into those hazel eyes, he saw confusion.

“No, Cas, I’m not finished yet.”

“Oh, I’m sorry.” Cas moved back to the middle of the bench. Unsure of what to do with his hands, he tried folding them in front of him, letting them hang at his side, holding them together in his lap, but everything just felt awkward and wrong.

“Cas, I think I can speak for Dean as well when I say that your self-assessment seemed pretty accurate, at least from what I know about you. A few of the things you said about us are true, too, but you seem to be looking at this whole thing wrong or incorrectly prioritizing what’s important to us.” Sam paused and waited silently until Cas met his gaze. When he did, he began to speak again almost instantly. “People know us, Cas. A lot of people got to know Dean because of football, and, yeah, we like talking and meeting people, but some other people just know us as the boys whose parents died when they were little.” Cas knew that Ellen wasn’t their biological mom, but Dean never mentioned their birth parents, and he never asked. That had Cas feeling guilty and ashamed, but Sam kept speaking. “I want to say this, Cas, and I hope you understand. And for the record, Dean  _ did _ tell me that he told you something similar, and while I thought it was maybe unnecessary for him to say it, the more I’ve gotten to know you, the more I think you need to hear it.” Again, he offered a brief pause. Cas had not dropped his eye contact, but sitting under Sam’s gaze was still making him uncomfortable. “Cas, reputation doesn’t mean anything. My older brother taught me a long time ago that if I can’t look myself in the eye and be proud of who I am, then nothing else matters.” With that, Sam glanced over at Dean, and Cas did as well. Dean was smiling back at his little brother, and giving his arm a loving squeeze.

When Sam turned back towards Cas, his expression was serious and sincere once again. “As much as a cisgendered white guy can, I understand your concern with people not respecting you because of your sexuality, and maybe even going so far as to being douches about you being gay, but Cas, your sexuality isn’t who you are. Dude, I’ve known you for two days, and over those two days, I’ve spent a couple hours with you where we’ve all just talked and whatever, and of all the things we’ve talked  _ about _ , none of us has talked about dating, or who we liked, or whatever. The same way Dean and I aren’t defined by who we like, neither are you. And put that aside,  _ so fucking what if you’re gay? _ ” Sam’s voice got loud. Several heads turned their direction, and although Cas ducked lower in his seat, hoping to avoid angry looks or heated comments, none were sent his way. “I have a crush on one of my best friends at school, and she doesn’t feel the same, but she knows how I feel about her, and we just keep moving forward. She didn’t stop talking to me or wanting to sit with me because of it; I just know that she doesn’t feel the same way, and that’s that.” Sam sighed. “Okay, I just said a  _ lot _ more than I intended, and I’m sorry for that, but dude, I hope you understand that Dean didn’t ask you to come here tonight, or to watch a movie with us, out of obligation; he did it because you’re a cool and funny guy, and we both wanna hang out with you.”

He never really knew where his insecurities stemmed from; they had always just been a part of him for as long as Cas could remember. In fact, he wished that he could blame a person or an event for sending him down that path, but no matter how hard he tried to find the cause of it all, he just ended up more worried that there was something fundamentally wrong with him. Charlie and Gabe had always been the most patient people when it came to helping him work through the seemingly endless levels of anxiety and self-doubt, but beyond them, he never really let anybody get close enough to see it all, and frankly, nobody ever tried. Until Dean, and then Sam.

Dean cleared his throat, drawing Cas’ attention. Looking into those beautiful green eyes made Cas instantly feel small. He felt his throat constricting as embarrassment began to sink in.  _ What the hell was I thinking? This was a terrible idea. I never should have opened my mouth. Why did I think that being honest here was the right thing to do? _ The more he worried, the tighter his chest began to feel, until the lights grew too bright and the music too loud. His heartbeat quickened as his eyes darted around the room to find the exit; although they hadn’t left their table, he couldn’t remember how to get out of the building, and the air was getting too thin for him to be able to breathe properly.

A warm hand met his shoulder, and from across the table, he saw Dean leaning towards him; Cas felt his bench seat shift beneath him as the added weight of Sam Winchester moved to his side. Sam slid an arm around Cas’ back as Dean continued to grip his shoulder, and although it wasn’t instantaneous, Cas felt himself relaxing. A minute passed, and then another, but neither brother spoke or moved from where they were; they simply allowed Cas to process and calm himself at his own pace.

Silent tears had trickled down his cheeks, and although he didn’t know when they appeared, they were leaving cold trails in their wake.

“Cas.” Dean’s voice was soft but hoarse, as though out of practice. “Cas, can you hear me?” Cas offered a small nod in reply. “Do you mind if I say something, and then ask something of you?” Again, he nodded. “Sammy’s right, Cas. I mean, with everything. The kid might be a twerp sometimes, but he just said what I was thinking better than I ever could’ve. I hope that you believe him--believe us both.”

Believing them was almost harder than not, because to believe them meant that he had to challenge the status quo and how he’d spent the last 18 years living. But how could he not? He knew what they looked like in their booth, with Dean reaching awkwardly across the table and gripping his shoulder, Sam leaning into his side, and him with blurry glasses and glistening cheeks. Someone who didn’t care about him wouldn’t do what they were doing, and deep down, Cas knew that. He appreciated that immensely.

“I do believe you, Dean.”

The hand on his shoulder squeezed reassuringly. “Okay. I’m glad. Then this is the part where I’m gonna ask something of you, and it’s actually two parts. First off, as we go forward, if you ever feel uncomfortable or like something isn’t right, will you tell us? Sammy and me, I mean? Whether it’s about us or not, can you tell us if something is going on and you’re just not feeling right?” Cas closed his eyes lightly, forcing the self-loathing aside to simply understand the request for what it was: a promise to reach out and ask for help. Yes, Cas could do that, and he said as much.

“Awesome. Then the second thing, and this may be harder for you to do, but I think it’s even more important at this point.”  _ How could anything possibly be harder than promising to tell the Winchesters when good ol’ self-doubt comes a-calling? _ “Cas, I need you to stop thinking that you’re a nuisance or embarrassing or whatever else for us. Unless we tell you otherwise, you need to assume that we want you around and that there are absolutely no problems going on here between the three of us. Like, at all. Can you promise me that?”  _ He’s right. I don’t know that I can promise this _ .

“Cas, this is important. I need you to promise me that you’ll stop assuming that Sammy and I have a problem with you, or are not being honest. I promise  _ you _ that we’ll tell you if something is getting to be too much for us, so you need to not jump the gun.” Cas took a slow breath, and then exhaled. Eventually, he nodded. What Dean was asking seemed impossible, but Cas knew that it wasn’t: ask for help if he needed help, and don’t assume that he’s a nuisance or obligation for them.

Dean gave his shoulder a final squeeze as Sam patted his back before sliding over, giving Cas a little more space for himself.

“Alright!” Dean’s voice returned to its usual level of confidence, and he clapped his hands together as though making some decision. “Back to the movie business then. Cas, you free on Friday?”

Cas fought the anxiety and the self-doubt and the insecurities; he forced himself to not think about the pathetic scene that he just made in the bar, surrounded by people who undoubtedly knew Dean and Sam, with this being their mom’s place; he disregarded the urge to freeze, or better yet, to run away as fast as he could and never look back. He was going to do what Dean asked of him, and remember that the boys wanted him around. For whatever reason, they liked him, and that thought gave Cas a little bit of hope.

“Yeah, Dean. I’m free on Friday.”


End file.
